Using Analytical Psychology as a theoretical basis, the present study aimed at clarifying and understanding the meanings that the man, who does not work, nor has an income of his own, attributes to himself, to his situation and to the social expectations related to working. Another objective was to elucidate which would be, in that case, the existing factors of investment and/or disinvestment in the work. Therefore, the study explored subjective aspects, using the qualitative approach and employing the Life History interview as a research tool. The research included four participants living in the state of São Paulo, Brazil. The inclusion criteria required that the participants be men, in the age group of approximate 30 years, without any paid work nor any type of income for at least five months, and financially dependent on their family members or spouses. The results show that the perception of work is an elementary configuration in the life trajectory. Work may signify a constant obligation — an imposition that endures — or be a meaning in transformation — leading to resignifications. The association between work and identity affirmation — as well as conscious and unconscious motivations — stands out. The research also made it possible to infer the existence of complexes resulting from the work experience. The survey of the subjective experiences linked to an increasingly prevailing conjuncture in the current society points to the intense affective load related to work. In this context, the assistance of the clinical psychologist becomes relevant.